(E)-dimethyl 2-(but-2-ynyl)-2-(hex-2-enyl)malonate | 1597562-86-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-dimethyl 2-(but-2-ynyl)-2-(hex-2-enyl)malonate
• CAS: 1597562-86-1
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: UYYBTDWUNSOAHB-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-dimethyl 2-(but-2-ynyl)-2-(hex-2-enyl)malonate 在 indium(III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.33h， 生成 (E)-dimethyl 3-(hex-2-en-2-yl)cyclopent-2-ene-1,1-dicarboxylate
  参考文献：
  名称：

  Mechanisms of the InCl₃-Catalyzed Type-I, II, and III Cycloisomerizations of 1,6-Enynes

  摘要：

  InCl3-catalyzed cycloisomerizations of 1,6-enynes can give either type-I dienes and cyclohexenes (type-III dienes), or type-II dienes, depending on the substitutions in the substrates. Previously, we studied how the type-II diene products were generated and found that the real catalytic species for the cycloisomerizations is InCl2+ (J. Org. Chem. 2012, 77, 8527-8540). In the present paper, we used density functional theory (DFT) calculations to reveal how the type-I and type-III dienes were generated. A unified model to explain how substituents affect the regiochemistry of type-I, II, and III cycloisomerizations has been provided. Experimental and computational investigation of the InCl3-catalyzed cycloisomerization of 1,6-enynes with both substituents at the alkyne and alkene parts has also been reported in the present study.

  DOI：

  10.1021/jo500059j
• 作为产物：
  描述：

  dimethyl 2-[(E)-hex-2-enyl]propanedioate 、 1-溴-2-丁炔 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 以71%的产率得到(E)-dimethyl 2-(but-2-ynyl)-2-(hex-2-enyl)malonate
  参考文献：
  名称：

  Mechanisms of the InCl₃-Catalyzed Type-I, II, and III Cycloisomerizations of 1,6-Enynes

  摘要：

  InCl3-catalyzed cycloisomerizations of 1,6-enynes can give either type-I dienes and cyclohexenes (type-III dienes), or type-II dienes, depending on the substitutions in the substrates. Previously, we studied how the type-II diene products were generated and found that the real catalytic species for the cycloisomerizations is InCl2+ (J. Org. Chem. 2012, 77, 8527-8540). In the present paper, we used density functional theory (DFT) calculations to reveal how the type-I and type-III dienes were generated. A unified model to explain how substituents affect the regiochemistry of type-I, II, and III cycloisomerizations has been provided. Experimental and computational investigation of the InCl3-catalyzed cycloisomerization of 1,6-enynes with both substituents at the alkyne and alkene parts has also been reported in the present study.

  DOI：

  10.1021/jo500059j